(Diethylamino)sulfur trifluoride → HCID 83854099, compound

HRID 2401211Notes

Reaction equation

CCN(S(F)(F)[F:7])CC.[Cl:10][C:11]1[N:16]=[CH:15][N:14]=[C:13]([CH:17](O)[CH3:18])[C:12]=1[CH3:20]>ClCCl>[Cl:10][C:11]1[C:12]([CH3:20])=[C:13]([CH:17]([F:7])[CH3:18])[N:14]=[CH:15][N:16]=1

Participants

Conditions

Temperature: -78 °C

Procedure

DAST (0.436 mL, 3.30 mmol) was added to dichloromethane (DCM) (11 mL), cooled to −78° C. and treated dropwise with a solution of 1-(6-chloro-5-methyl-4-pyrimidinyl)ethanol (Intermediate 44, 380 mg, 2.201 mmol) in DCM (4 mL) under argon. The resulting mixture was allowed to warm to room temperature and stirred for 4 hours. The reaction was quenched by adding water (7 ml) and extracted with DCM (×2). The DCM layers were separated, combined, dried under magnesium sulfate and evaporated under reduced pressure. The residue was purified by SP4 Biotage column chromatography eluting with a gradient of 0-20% ethyl acetate and iso-hexane. Product containing fractions were combined and evaporated under reduced pressure to give the title compound as a colourless oil (153 mg);

Workup

temperatureto warm to room temperature
customThe reaction was quenched
additionby adding water (7 ml)
extractionextracted with DCM (×2)
customThe DCM layers were separated
customdried under magnesium sulfate
customevaporated under reduced pressure
customThe residue was purified by SP4 Biotage column chromatography
washeluting with a gradient of 0-20% ethyl acetate and iso-hexane
additionProduct containing fractions
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-90bed13ea5264f6aaaa4ce793b84de81
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796283B2

Reaction notes

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